트리메틸실릴케텐

트리메틸실릴케텐
트리메틸실릴케텐 구조식 이미지
카스 번호:
4071-85-6
한글명:
트리메틸실릴케텐
동의어(한글):
트리메틸실릴케텐
상품명:
Trimethylsilylketene
동의어(영문):
Trimethylsilylketene;(Trimethylsilyl)ketene;(trimethylsilyl)-ethenon;2-trimethylsilylethenone;(TRIMETHYLSILYL)KETENE 97;(TRIMETHYLSILYL)KETENE 97%;Ethenone, 2-(trimethylsilyl)-;2-(Trimethylsilyl)ethene-1-one
CBNumber:
CB1500224
분자식:
C5H10OSi
포뮬러 무게:
114.22
MOL 파일:
4071-85-6.mol

트리메틸실릴케텐 속성

끓는 점
80-82 °C(lit.)
밀도
0.813 g/mL at 25 °C(lit.)
굴절률
n20/D 1.413(lit.)
인화점
3 °F
용해도
Sol CH2Cl2, CHCl3, CCl4, THF, diethyl ether, and most standard organic solvents; reacts with alcoholic and amine solvents.
EPA
Ethenone, (trimethylsilyl)- (4071-85-6)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 F
위험 카페고리 넘버 11
안전지침서 7/9-16-29-33
유엔번호(UN No.) UN 1993 3/PG 2
WGK 독일 3
그림문자(GHS): GHS hazard pictograms
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H225 고인화성 액체 및 증기 인화성 액체 구분 2 위험 GHS hazard pictograms P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
예방조치문구:
P210 열·스파크·화염·고열로부터 멀리하시오 - 금연 하시오.
P233 용기를 단단히 밀폐하시오. 용기는 환기가 잘 되는 곳에 단단히 밀폐하여 보관하시오.
P240 용기와 수용설비를 접지 및 접합시키시오.
P241 폭발 방지용 장비[전기적/환기/조명/...]을(를) 사용하시오.
P242 스파크가 발생하지 않는 도구를 사용하시오
P243 정전기 방지 조치를 취하시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P303+P361+P353 피부(또는 머리카락)에 묻으면 오염된 모든 의복은 벗거나 제거하시오 피부를 물로 씻으시오/샤워하시오.
P370+P378 화재 시 불을 끄기 위해 (Section 5. 폭발, 화재시 대처방법의 적절한 소화제)을(를) 사용하시오.
P403+P235 환기가 잘 되는 곳에 보관하고 저온으로 유지하시오.
P501 ...에 내용물 / 용기를 폐기 하시오.

트리메틸실릴케텐 C화학적 특성, 용도, 생산

물리적 성질

bp 81–82 °C; d 0.80 g cm?3.

용도

Trimethylsilylketene is a reactive acylating agent for amines and alcohols; building block for synthesis of coumarins; synthesis of α-silyl ketones via the addition of organocerium reagents; treatment with stabilized ylides forms trimethylsilyl-substituted allenes;a cycloaddition with aldehydes affords β-lactones; forms small rings with diazomethane; treatment with n-BuLi forms a ketene enolate. It participates in the reactions of Trimethylsilylacetylation of Alcohols and Amines, Synthesis of Coumarins via Cyclization–Elimination, One-pot Formation of α-Silyl Ketones, Preparation of Trimethylsilyl-Substituted Allenes, Preparation of β-Lactones, Reaction with Diazomethane to Form Silylated Cyclopropanes and Cyclobutanones, Synthesis of Heterocycles, Formation of the Ketene Enolate, and other uses.

제조 방법

Most often prepared (eq 1) by pyrolysis of ethoxy(trimethylsilyl)acetylene at 120??C (100 mmol scale, 65% yield).Recently, pyrolysis of t-butoxy(trimethylsilyl) acetylene has been shown to be a convenient alternative for the preparation of trimethylsilylketene (1). Thermal decomposition of t-butoxy(trimethylsilyl)acetylene causes elimination of 2-methylpropene slowly at temperatures as low as 50??C and instantaneously at 100¨C110??C (30 mmol scale, 63% yield). The main advantage of this method is that it is possible to generate trimethylsilylketene in the presence of nucleophiles, leading to in situ trimethylsilylacetylation (eq 2). Increased shielding of the triple bond prevents problems such as polymerization and nucleophilic attack that occur when the ketene is generated in situ from (trimethylsilyl)ethoxyacetylene. Trimethylsilylketene can also be prepared (eq 3) via the dehydration of commercially available trimethylsilylacetic acid with 1,3- dicyclohexylcarbodiimide (DCC) in the presence of a catalytic amount of triethylamine (100 mmol scale, 63%). Other typical methods used for ketene generation such as dehydrohalogenation of the acyl chloride and pyrolysis of the anhydride have been applied to the preparation of (1); however, both methods afford low yields.

4071-85-6 synthesis

There have been no significant developments in the methods used to prepare trimethylsilylketene (TMSK). However, Black et al. have published slight modifications. to the original preparation by Ruden, which primarily deals with accessing ethoxyacetylene.

트리메틸실릴케텐 준비 용품 및 원자재

원자재

준비 용품


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